An Orthogonally Protected Cyclitol for the Construction of Nigerose- and Dextran-Mimetic Cyclophellitols

[Image: see text] Cyclophellitols are potent inhibitors of exo- and endoglycosidases. Efficient synthetic methodologies are needed to fully capitalize on this intriguing class of mechanism-based enzyme deactivators. We report the synthesis of an orthogonally protected cyclitol from d-glucal (19% yie...

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Autores principales: Ofman, Tim P., Küllmer, Florian, van der Marel, Gijsbert A., Codée, Jeroen D. C., Overkleeft, Herman S.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8689644/
https://www.ncbi.nlm.nih.gov/pubmed/34846911
http://dx.doi.org/10.1021/acs.orglett.1c03723
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author Ofman, Tim P.
Küllmer, Florian
van der Marel, Gijsbert A.
Codée, Jeroen D. C.
Overkleeft, Herman S.
author_facet Ofman, Tim P.
Küllmer, Florian
van der Marel, Gijsbert A.
Codée, Jeroen D. C.
Overkleeft, Herman S.
author_sort Ofman, Tim P.
collection PubMed
description [Image: see text] Cyclophellitols are potent inhibitors of exo- and endoglycosidases. Efficient synthetic methodologies are needed to fully capitalize on this intriguing class of mechanism-based enzyme deactivators. We report the synthesis of an orthogonally protected cyclitol from d-glucal (19% yield over 12 steps) and its use in the synthesis of α-(1,3)-linked di- and trisaccharide dextran mimetics. These new glycomimetics may find use as Dextranase inhibitors, and the developed chemistries in widening the palette of glycoprocessing enzyme-targeting glycomimetics.
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spelling pubmed-86896442021-12-22 An Orthogonally Protected Cyclitol for the Construction of Nigerose- and Dextran-Mimetic Cyclophellitols Ofman, Tim P. Küllmer, Florian van der Marel, Gijsbert A. Codée, Jeroen D. C. Overkleeft, Herman S. Org Lett [Image: see text] Cyclophellitols are potent inhibitors of exo- and endoglycosidases. Efficient synthetic methodologies are needed to fully capitalize on this intriguing class of mechanism-based enzyme deactivators. We report the synthesis of an orthogonally protected cyclitol from d-glucal (19% yield over 12 steps) and its use in the synthesis of α-(1,3)-linked di- and trisaccharide dextran mimetics. These new glycomimetics may find use as Dextranase inhibitors, and the developed chemistries in widening the palette of glycoprocessing enzyme-targeting glycomimetics. American Chemical Society 2021-11-30 2021-12-17 /pmc/articles/PMC8689644/ /pubmed/34846911 http://dx.doi.org/10.1021/acs.orglett.1c03723 Text en © 2021 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Ofman, Tim P.
Küllmer, Florian
van der Marel, Gijsbert A.
Codée, Jeroen D. C.
Overkleeft, Herman S.
An Orthogonally Protected Cyclitol for the Construction of Nigerose- and Dextran-Mimetic Cyclophellitols
title An Orthogonally Protected Cyclitol for the Construction of Nigerose- and Dextran-Mimetic Cyclophellitols
title_full An Orthogonally Protected Cyclitol for the Construction of Nigerose- and Dextran-Mimetic Cyclophellitols
title_fullStr An Orthogonally Protected Cyclitol for the Construction of Nigerose- and Dextran-Mimetic Cyclophellitols
title_full_unstemmed An Orthogonally Protected Cyclitol for the Construction of Nigerose- and Dextran-Mimetic Cyclophellitols
title_short An Orthogonally Protected Cyclitol for the Construction of Nigerose- and Dextran-Mimetic Cyclophellitols
title_sort orthogonally protected cyclitol for the construction of nigerose- and dextran-mimetic cyclophellitols
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8689644/
https://www.ncbi.nlm.nih.gov/pubmed/34846911
http://dx.doi.org/10.1021/acs.orglett.1c03723
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